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Information on EC 1.6.5.9 - NADH:quinone reductase (non-electrogenic)
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1.6.5.9 NADH:quinone reductase (non-electrogenic)IUBMB Comments
A flavoprotein (FAD or FMN). Occurs in mitochondria of yeast and plants, and in aerobic bacteria. Has low activity with NADPH. Unlike EC 7.1.1.2, NADH:ubiquinone reductase (H+-translocating), this enzyme does not pump proteons of sodium ions across the membrane. It is also not sensitive to rotenone.
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Word Map
- 1.6.5.9
- ndh-2
- hydrogenases
-
proton-translocating
- ubiquinone-1
- hqno
- 2-heptyl-4-hydroxyquinoline-n-oxide
-
single-subunit
- deamino-nadh
-
na+-translocating
-
rotenone-sensitive
The expected taxonomic range for this enzyme is: Eukaryota, Bacteria
Synonyms
nadh:quinone oxidoreductase, alternative nadh dehydrogenase, rotenone-insensitive nadh dehydrogenase, nadh dehydrogenase-2, ndh2e, nadh:q6 oxidoreductase, internal alternative nadh dehydrogenase, ndh2i, alternative nadh-quinone oxidoreductase, non-proton-pumping nadh dehydrogenase, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
alternative NADH dehydrogenase
alternative NADH:quinone reductase
alternative NADH:ubiquinone oxidoreductase
alternative rotenone-insensitive NADH:Q oxidoreductase
CathTA2_0279
Cgl1465
EC 1.6.5.11
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-
formerly
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EC 1.6.99.5
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formerly
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external alternative NADH dehydrogenase
external NADH:ubiquinone oxidoreductase
external rotenone-insensitive NADH dehydrogenase
internal rotenone-insensitive NADH dehydrogenase
NADH: ubiquinone-2 oxidoreductase
NADH:ubiquinone reductase (non-electrogenic)
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-
-
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NADHQ2
NDA
NDB
NDH
NDH-II
NDH2
NDH2e
NDH2i
Ndi1
non-proton pumping type II NADH dehydrogenase
non-proton-pumping NADH dehydrogenase
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
NADH + H+ + a quinone = NAD+ + a quinol
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-
-
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PATHWAY SOURCE
PATHWAYS
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, , , , ,
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SYSTEMATIC NAME
IUBMB Comments
NADH:quinone oxidoreductase
A flavoprotein (FAD or FMN). Occurs in mitochondria of yeast and plants, and in aerobic bacteria. Has low activity with NADPH. Unlike EC 7.1.1.2, NADH:ubiquinone reductase (H+-translocating), this enzyme does not pump proteons of sodium ions across the membrane. It is also not sensitive to rotenone.
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CAS REGISTRY NUMBER
COMMENTARY
9028-04-0
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
NADH + H+ + 2,6-dichlorophenolindophenol
NAD+ + reduced 2,6-dichlorophenolindophenol
-
-
-
-
?
NADH + H+ + 2-azido-5-geranyl-3-methoxy-6-methyl-1,4-benzoquinone
NAD+ + 2-azido-5-geranyl-3-methoxy-6-methyl-1,4-benzoquinol
-
-
-
?
NADH + H+ + duroquinone
NAD+ + duroquinol
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49% activity compared to ubiquinone-1
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-
?
NADH + H+ + N-(6-[[(4E,8E)-10-(4-azido-5-methoxy-2-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl)-4,8-dimethyldeca-4,8-dien-1-yl]amino]-6-oxohexyl)-6-([5-[(3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl]pentanoyl]amino)hexanamide
NAD+ + N-(6-[[(4E,8E)-10-(4-azido-3,6-dihydroxy-5-methoxy-2-methylcyclohexa-1,4-dien-1-yl)-4,8-dimethyldeca-4,8-dien-1-yl]amino]-6-oxohexyl)-6-([5-[(3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl]pentanoyl]amino)hexanamide
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-
-
?
NADH + H+ + N-[(4E,8E)-10-(4-azido-5-methoxy-2-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl)-4,8-dimethyldeca-4,8-dien-1-yl]-6-([5-[(3aS,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl]pentanoyl]amino)hexanamide
NAD+ + N-[(4E,8E)-10-(4-azido-3,6-dihydroxy-5-methoxy-2-methylcyclohexa-1,4-dien-1-yl)-4,8-dimethyldeca-4,8-dien-1-yl]-6-([5-[(3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl]pentanoyl]amino)hexanamide
-
-
-
?
NADH + H+ + N-[2-[2-(2-[[(4E,8E)-10-(4-azido-5-methoxy-2-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl)-4,8-dimethyldeca-4,8-dien-1-yl]oxy]ethoxy)ethoxy]ethyl]-5-[(3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl]pentanamide
NAD+ + N-[2-[2-(2-[[(4E,8E)-10-(4-azido-3,6-dihydroxy-5-methoxy-2-methylcyclohexa-1,4-dien-1-yl)-4,8-dimethyldeca-4,8-dien-1-yl]oxy]ethoxy)ethoxy]ethyl]-5-[(3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl]pentanamide
-
-
-
?
2 ferricyanide + NADH
2 ferrocyanide + NAD+ + H+
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15% activity compared to ubiquinone-1
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-
?
NADH + H+ + 2,6-dichloroindophenol
NAD+ + reduced 2,6-dichloroindophenol
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17% activity compared to ubiquinone-1
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-
?
NADH + H+ + 2,6-dichloroindophenol
NAD+ + reduced 2,6-dichloroindophenol
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-
-
-
?
NADH + H+ + menadione
NAD+ + menadiol
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47% activity compared to ubiquinone-1
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-
?
NADH + H+ + ubiquinone-2
NAD+ + ubiquinol-2
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ubiquinone is the best electron acceptor
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?
additional information
?
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NDH-II does not pump protons
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?
additional information
?
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the yeast enzyme is a two-electron reaction enzyme
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-
?
additional information
?
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NAD+ binds in the second Rossmann domain in a predominantly positively charged cleft, with the nicotinamide ring approaching the re-face of the FAD
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-
?
additional information
?
-
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the alternative NADH:ubiquinone oxidoreductase does not contribute to the proton gradient across the respiratory membrane
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?
additional information
?
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alternative NADH:ubiquinone oxidoreductase does not pump protons across the inner mitochondrial membrane
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?
additional information
?
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NDH2 does not translocate protons across the inner mitochondrial membrane
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?
additional information
?
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NDH2e is a peripheral single-subunit oxido-reductase that does not pump protons
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?
additional information
?
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NDH2e is a peripheral single-subunit oxido-reductase that does not pump protons
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?
additional information
?
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alternative NADH:ubiquinone oxidoreductase does not pump protons across the inner mitochondrial membrane
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-
?
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NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
additional information
?
-
-
the alternative NADH:ubiquinone oxidoreductase does not contribute to the proton gradient across the respiratory membrane
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-
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
FAD
-
the enzyme contains one molecule of noncovalently bound FAD as redox cofactor
FAD
-
binding site structure, overview. The isoalloxazine ring of the FAD is positioned between the two Rossmann domains, which define two channels along the interdomain plane that lead to the active site
NADH
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the enzyme is specific for NADH. NADPH or deamino-NADH show rates that are at least 250times lower than obtained with NADH at any pH between 5.5 and 8.5
NADH
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small NADH binding domain within a larger FAD binding domain at amino acid positions 226-334
additional information
Ndi1 contains no iron-sulfur cluster
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additional information
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the enzyme contains no iron-sulfur clusters
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additional information
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the mature enzyme contains no iron-sulfur clusters
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
AMP
-
dead end reversible inhibitor, competitive inhibitor of NADH and uncompetitive inhibitor of 2,6-dichlorophenolindophenol
aurachin C 1-10
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12% residual activity at 0.01 mM, noncompetitive inhibitor
mangostin
20 microM, 19% residual activity for detergent-solubilized enzyme
morin
20 microM, 32% residual activity for detergent-solubilized enzyme, 18.7% residual activity for lipid-reconstituted enzyme
nordihydroguaiaretic acid
20 microM, 33% residual activity for detergent-solubilized enzyme, 18.7% residual activity for lipid-reconstituted enzyme
piceatannol
20 microM, 35% residual activity for detergent-solubilized enzyme
rotenone
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three NADH dehydrogenases, two external rotenone-insensitive NADH:ubiquinone oxidoreductases (NDE1 and NDE2), and one internal rotenone-insensitive NADH:ubiquinone reductase (NDI1)
scopafungin
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33% residual activity at 0.005 mg/ml, noncompetitive inhibitor
tyrphostin AG 537
20 microM, 22% residual activity for detergent-solubilized enzyme, 57% residual activity for lipid-reconstituted enzyme
tyrphostin AG 808
20 microM, 7% residual activity for detergent-solubilized enzyme
additional information
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the enzyme is not inhibited by rotenone, and activity is not affected by EDTA (1 mM), EGTA (1 mM) or Ca2+ or Mg2+ (1 mM)
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additional information
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NAD+, Mg-ADP, Mg-ATP, Ca2+ (all at 2 mM) or piericidin, rotenone (both at 0.01 mM) or adenosyl-3'-O-[3-[N-(4-azido-2-nitrophenyl)-amino]propionyl]-NAD+ (0.05 mM) are without inhibitory or stimulatory effects
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additional information
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not inhibited by rotenone, NAD+ does not inhibit the activity of the enzyme, even at concentrations as high as 10 mM
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additional information
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NADH oxidation is completely insensitive to amytal and rotenone
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additional information
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not inhibited by piericidin A. Addition of up to 10% (v/v) ethanol has no effect on NADH:NBQ oxidoreductase activity
-
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
1-hexadecyl-3-(trifluoroethyl)-sn-glycero-2-phosphomethanol
20 microM, 149% of initial activity for detergent-solubilized enzyme
17-beta-hydroxy-17-alpha-ethynyl-delta-4-androstano[3,2-b]pyrimido[1,2-a]benzimidazole
20 microM, 142% of initial activity for detergent-solubilized enzyme
2,6-difluoro-4-[2-(phenylsulfonylamino)ethylthio]phenoxyacetamide
20 microM, 136% of initial activity for detergent-solubilized enzyme, 134% of initial activity for lipid-reconstituted enzyme
pentylenetetrazole
20 microM, 132% of initial activity for detergent-solubilized enzyme
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DISEASE
TITLE OF PUBLICATION
LINK TO PUBMED
Infections
Regulation of the mechanism of Type-II NADH: Quinone oxidoreductase from S. aureus.
Leishmaniasis
An Essential Type I Nitroreductase from Leishmania major Can Be Used to Activate Leishmanicidal Prodrugs.
Mitochondrial Diseases
Alternative NAD(P)H dehydrogenase and alternative oxidase: Proposed physiological roles in animals.
Mitochondrial Diseases
Iron-sulfur cluster N5 is coordinated by an HXXXCXXCXXXXXC motif in the NuoG subunit of Escherichia coli NADH:quinone oxidoreductase (complex I).
nadh:ubiquinone reductase (h+-translocating) deficiency
Molecular Gene Therapy: Overexpression of the Alternative NADH Dehydrogenase NDI1 Restores Overall Physiology in a Fungal Model of Respiratory Complex I Deficiency.
Parkinson Disease
Parkinson's disease and mitochondrial complex I: a perspective on the Ndi1 therapy.
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.0181
N-(6-[[(4E,8E)-10-(4-azido-5-methoxy-2-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl)-4,8-dimethyldeca-4,8-dien-1-yl]amino]-6-oxohexyl)-6-([5-[(3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl]pentanoyl]amino)hexanamide
in 50 mM sodium phosphate buffer (pH 6.0) and 1 mM EDTA, temperature not specified in the publication
0.022
N-[(4E,8E)-10-(4-azido-5-methoxy-2-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl)-4,8-dimethyldeca-4,8-dien-1-yl]-6-([5-[(3aS,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl]pentanoyl]amino)hexanamide
in 50 mM sodium phosphate buffer (pH 6.0) and 1 mM EDTA, temperature not specified in the publication
0.033
N-[2-[2-(2-[[(4E,8E)-10-(4-azido-5-methoxy-2-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl)-4,8-dimethyldeca-4,8-dien-1-yl]oxy]ethoxy)ethoxy]ethyl]-5-[(3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl]pentanamide
in 50 mM sodium phosphate buffer (pH 6.0) and 1 mM EDTA, temperature not specified in the publication
0.0152
ubiquinone-1
in 50 mM sodium phosphate buffer (pH 6.0) and 1 mM EDTA, temperature not specified in the publication
0.0079
ubiquinone-2
in 50 mM sodium phosphate buffer (pH 6.0) and 1 mM EDTA, temperature not specified in the publication
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.031
NADH
-
using ubiquinone-2 as substrate, in 20 mM MOPS/KOH, 1 mM EDTA, 0.03% (v/v) Triton X-100, 200 mM KCl, pH 6.2, temperature not specified in the publication
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Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
11.5
AMP
-
linear uncompetitive inhibition of 2,6-dichlorophenolindophenol, pH 7.0, 25°C
0.0054
flavone
-
hyperbolic uncompetitive inhibition of NADH, pH 7.0, 25°C
0.0071
flavone
-
hyperbolic noncompetitive inhibition of 2,6-dichlorophenolindophenol, pH 7.0, 25°C
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IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.0017
1-hydroxy-2-dodecyl-4(1H)quinolone
Gluconobacter oxydans
-
at 25°C in 100mM Tris-HCl (pH 7.4)
0.095
flavone
Saccharomyces cerevisiae
-
using ubiquinone-2 as substrate, in 20 mM MOPS/KOH, 1 mM EDTA, 0.03% (v/v) Triton X-100, 200 mM KCl, pH 6.2, temperature not specified in the publication
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
0.78
-
crude extract, using ubiquinone-2 as substrate, at pH 6.2, temperature not specified in the publication
1671
-
after 2134fold purification, using ubiquinone-2 as substrate, at pH 6.2, temperature not specified in the publication
61.9
-
after 2134fold purification, using ubiquinone-6 as substrate, at pH 6.2, temperature not specified in the publication
69.2
-
after 18.7fold purification, using ubiquinone-1 as substrate, at 25°C and pH 7.2
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
6.2
-
with ubiquinone-2 as acceptor a sharp maximum at pH 6.2 is obtained
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pH RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
4.5 - 9.5
-
with ubiquinone-6 as acceptor the activity is almost constant between pH 4.5 and 9.5, at pH values lower than 4.5 and higher than 9.5, enzymic activity is irreversibly destroyed
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pI VALUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
genes ndeA-B and ndiA encoding external and internal alternative NADH dehydrogenases
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brenda